Shelter Island Hotel Guide - Hotels with Pool in Shelter Island, New York

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Check availability on Shelter Island Hotels with Pool

Our top choices for Shelter Island hotels with a pool

Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (302 reviews)
"The room was comfortable and clean. A good value for the money."
United States
Michael
The price is €76
includes taxes & fees
23 Feb - 24 Feb
Clinton Motel
Outdoor pool

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (106 reviews)
"Hotel was beautiful !!"
United States
Erica
The price is €161
includes taxes & fees
5 Mar - 6 Mar
Offshore Montauk
Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,008 reviews)
"Hotel was very clean, staff was wonderful and the pool was so relaxing. It was a quick visit but definitely would stay again if I was in that area. "
United States
Kathleen
The price is €95
includes taxes & fees
26 Feb - 27 Feb
Quality Inn Old Saybrook - Westbrook
Seasonal outdoor pool

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (305 reviews)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
The price is €151
includes taxes & fees
22 Feb - 23 Feb
Windward Shores Ocean Resort
Exterior

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,297 reviews)
"Nice pool, great restaurant "
United States
April
The price is €194
includes taxes & fees
7 Mar - 8 Mar
Montauk Manor
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (452 reviews)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is €95
includes taxes & fees
22 Feb - 23 Feb
Hamlet Inn
Individually decorated, individually furnished, desk, laptop workspace

Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
Old Saybrook
7.2 out of 10, Good, (466 reviews)
"All good it met our expectations as a budget hotel. Large clean room bed was comfortable although the pillows were past it. "
United States
Hilary
The price is €65
includes taxes & fees
3 Mar - 4 Mar
Econo Lodge Inn & Suites Old Saybrook Westbrook
Exterior

Southampton Long Island Hotel

Southampton Long Island Hotel
2.5 star property
Southampton
8.6 out of 10, Excellent, (207 reviews)
"Staff was amazing. The room was very clean. I've stayed here numerous times, even on the night before my wedding as I was married in the Hamptons and I highly recommend! "
United States
Martine
The price is €106
includes taxes & fees
21 Feb - 22 Feb
Southampton Long Island Hotel
Seasonal outdoor pool, pool umbrellas, pool loungers

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very good, (888 reviews)
"Big room Clean Needs bathroom update In general, we had a good day"
United States
Raz
Kenny's Tipperary Inn
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool loungers

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (567 reviews)
"Lovely hotel with great location in town. Great free breakfast and wonderful staff. We will return! "
United States
Pamela
The price is €148
includes taxes & fees
5 Mar - 6 Mar
The Harbor Front Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Shelter Island

Breakfast included
Sea view

Top Shelter Island Hotel Reviews

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

10/10 Excellent
"Clean room, good breakfast "
Mary 1-night trip
Posted 2 days ago
Quality Inn Old Saybrook - Westbrook

Frequently asked questions

What are some accommodation options with pools in Shelter Island?
Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool and a private beach. Sound View Greenport: Offers a private beach, a seasonal outdoor pool and 2 bars. Montauk Manor: Aparthotel, 14-minute walk from The Hamptons Beaches. Provides a seasonal outdoor pool, an indoor pool and 3 outdoor tennis courts. Montauk Blue Hotel: Hotel, 1-minute walk from The Hamptons Beaches. Features sunloungers, an indoor pool and complimentary wireless Internet access. Water's Edge Resort & Spa: Offers a seasonal outdoor pool, an indoor pool and a private beach.
What is there to see and do in Shelter Island?
Surround yourself with nature at Sunset Beach and Mashomack Preserve. Discover sights such as Shelter Island Historical Society, Shelter Island Whale's Tail and Crescent Beach during your stay.
When is the best time to book a hotel with a pool in Shelter Island?
You may want to think about accommodation that has an outdoor pool if you'll be visiting Shelter Island in the hottest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be what you want if you come to town during the coldest months of January, February or March, when the average temperature is 3°C.